The ruthenium(II)-catalyzed direct ring-opening reaction of 7-azabenzonorbornadienes with anilides via C-H activation to access hydronaphthylamines has been developed. The transformation proceeds with a high stereoselectivity to give cis-configuration products under redox-neutral conditions.
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http://dx.doi.org/10.1021/acs.joc.8b00604 | DOI Listing |
Organometallics
July 2024
Department of Chemistry, Colgate University, 13 Oak Drive, Hamilton, New York 13346, United States.
In this article, we report the development of ruthenium-catalyzed hydrogenolysis of epoxides to selectively give the branched (Markovnikov) alcohol products. In contrast to previously reported catalysts, the use of Milstein's PNN-pincer-ruthenium complex at room temperature allows the conversion of enantiomerically enriched epoxides to secondary alcohols without racemization of the product. The catalyst is effective for a range of aryl epoxides, alkyl epoxides, and glycidyl ethers and is the first homogeneous system to selectively promote hydrogenolysis of glycidol to 1,2-propanediol, without loss of enantiomeric purity.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2024
Beijing National Laboratory of Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing, 100871, China.
Nat Commun
January 2024
National Institute of Biological Sciences, 7 Science Park Road, Zhongguancun Life Science Park, Beijing, 102206, China.
Tetrodotoxin and congeners are specific voltage-gated sodium channel blockers that exhibit remarkable anesthetic and analgesic effects. Here, we present a scalable asymmetric syntheses of Tetrodotoxin and 9-epiTetrodotoxin from the abundant chemical feedstock furfuryl alcohol. The optically pure cyclohexane skeleton is assembled via a stereoselective Diels-Alder reaction.
View Article and Find Full Text PDFACS Org Inorg Au
August 2023
Department of Chemistry, Stony Brook University, Stony Brook, New York 11794-3400, United States.
We report an investigation of rates of ruthenium-catalyzed alternating ring opening metathesis (AROM) of cyclohexene with two different Ru-cyclohexylidene carbenes derived from bicyclo[4.2.0]oct-6-ene-7-carboxamides (A monomer) that bear different side chains.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
August 2023
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, 600 Dunyu Road, Hangzhou, 310030, Zhejiang Province, China.
Activation of C-C bonds allows editing of molecular skeletons, but methods for selective activation of nonpolar C-C bonds in the absence of a chelation effect or a driving force derived from opening of a strained ring are scarce. Herein, we report a method for ruthenium-catalyzed activation of nonpolar C-C bonds of pro-aromatic compounds by means of π-coordination-enabled aromatization. This method was effective for cleavage of C-C(alkyl) and C-C(aryl) bonds and for ring-opening of spirocyclic compounds, providing an array of benzene-ring-containing products.
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